methyl (3S,4R,5R)-5-acetoxy-3-azido-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

Base Information

Chemical Name:methyl (3S,4R,5R)-5-acetoxy-3-azido-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate
CAS No.:352533-31-4
Molecular Formula:C₁₁H₁₅N₃O₇S
Molecular Weight:333.322
Hs Code.:

Synonyms:methyl (3S,4R,5R)-5-acetoxy-3-azido-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

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Chemical Property of methyl (3S,4R,5R)-5-acetoxy-3-azido-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

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Technology Process of methyl (3S,4R,5R)-5-acetoxy-3-azido-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

There total 10 articles about methyl (3S,4R,5R)-5-acetoxy-3-azido-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

: 124-63-0
methanesulfonyl chloride

: 352533-29-0
methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate

: 352533-31-4
methyl (3S,4R,5R)-5-acetoxy-3-azido-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0008-6215(01)00079-9

Reference yield:

: 88165-26-8
methyl 3,4-O-isopropylideneshikimate

: 352533-31-4
methyl (3S,4R,5R)-5-acetoxy-3-azido-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / pyridine / 1 h / 20 °C

2: 97 percent / SOCl₂; Et₃N / tetrahydrofuran / 3 h / 20 °C

3: 17 mg / pyridine / 1 h / 20 °C

4: 92 percent / NaN₃ / dimethylformamide / 20 h / 20 °C

5: 72 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With pyridine; thionyl chloride; sodium azide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00079-9

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 352533-31-4
methyl (3S,4R,5R)-5-acetoxy-3-azido-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / H₂SO₄ / 20 °C

2: 47 percent / pyridine / 2 h / 20 °C

3: 61 percent / SOCl₂ / pyridine / 2 h / 20 °C

4: 92 percent / H₂SO₄ / methanol / 20 °C

5: 92 mg / Dowex-50 (H+) / acetone / 3 h / 20 °C

6: 100 percent / pyridine / 1 h / 20 °C

7: 97 percent / SOCl₂; Et₃N / tetrahydrofuran / 3 h / 20 °C

8: 17 mg / pyridine / 1 h / 20 °C

9: 92 percent / NaN₃ / dimethylformamide / 20 h / 20 °C

10: 72 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With pyridine; thionyl chloride; sodium azide; Dowex-50 (H+); sulfuric acid; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(01)00079-9